Sodium Hydroxide → 5-tert-Butyl-isophthalic acid monomethyl ester

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Reaction Steps

To a solution of dimethyl 5-tert-butylisophthalate (93.3 g, 0.373 mol) in MeOH (610 mL) was added a solution of sodium hydroxide (14.9 g, 0.373 mol) in water (41 mL) at 25 ° C. The mixture was allowed to stir at this temperature for 4 h and then concentrated. The residue was suspended in 1M H2SO4 and filtered. The solid was washed with water and dried under vacuum to give 3-tert-butyl-5-(methoxycarbonyl)benzoic acid (92 g) as a white solid which was used without purification. 1H NMR (400 MHz, d6-DMSO) δ: 8.35 (s, 1H), 8.20 (m, 2H), 3.85 (s,3H), and 1.30 (s, 9H). LCMS: ES− 235.4.

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